One of my friends feels like they don't know very much about what's going on in the world. this is my attempt to bring them up to speed, as best I can.
These are short, well-written, and substantial. They are snapshots, not the total picture.
The Last Question by Isaac Asimov
This short science-fiction story has always stuck with me. It has an unparalleled vision of where we came from, where we are, and where we might going, in under 10 pages.
Global Economic History: A Very Short Introduction by Robert Allen Attempts to explain why the Industrial Revolution happened when and where it did (England, 1700s). The Industrial Revolution is basically why Europe and North America are rich and powerful now, while Asia, Africa, and South America are poor and weak.
Slaughterhouse-Five by Kurt Vonnegut
Vonnegut is my favorite author. He fought in World War II. Slaughterhouse-Five is his fictionalized account of what happened. World War II is the pivotal event of the 20th century; it's probably the most important thing to understand in modern history. There are more comprehensive books about WWII, but this is a short one. And fun to read!
The Prince by Niccoló Macchiavelli
Modern political theory starts with Locke, Hobbes, and Macchiavelli. Understanding some political theory is important because it gives frameworks for understanding present-day political behavior. And there is a lot of political behavior in business, social circles, and politics (duh). The Prince is short and sweet. Skip the introduction, it's not very interesting.
I wouldn't try to follow all the news, or all the outlets. I would follow some good ones, some of the time (as much as is interesting). If it isn't interesting, don't read it.
The New York Times is probably the best place to start. And it publishes a ton of content. I read something from it everyday.
Vox is a new outlet. It updates more frequently than the traditional papers, and can be a little gossipy. It is very up-to-date, and usually has something fun to read.
The Economist is a British paper with an economic focus (duh, again). It often has really good stories, and gives a European perspective that can be interesting. I think there is a paywall after a couple of articles/month.
That's probably a good start.
[rereads: 2, edits: changed some links]